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JEE Main levelSingle correct optionDifficulty 2 of 3g2124

An ether solution of aniline, phenol and naphthalene is shaken with dilute aqueous $HCl$ . Which compound passes into the aqueous layer?

APhenol, as phenoxide
BNaphthalene, as its salt
CBoth aniline and phenol
DAniline, as anilinium chloride

Answer: D

Aniline is a base (conjugate acid

p K_{a}

4.6) and is protonated by strong acid

HCl

to the water-soluble

C X_{6} H X_{5} NH X_{3} X^{+} Cl X^{-}

. Phenol is a very weak base and naphthalene is not basic, so both stay in the ether.

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